Both superintendents and principals create a foundation for student achievement, school culture, and the vision of a school building or district. When combined, these two, distinct administrative roles become one unique position with less time and resources to fulfill individual job responsibilities. This comparative case study was designed to foster understanding of rural dual-role administrators' roles, responsibilities, and experiences. A dual-role administrator was defined as an individual serving as a superintendent and principal simultaneously. By interviewing and observing two practitioners and reviewing public documents, this study developed an in-depth investigation of the cases. As a result of this study, there is an increased understanding of the day-to-day operations of dual-role administrators. This research added to the literature by understanding dual-role administrators from a situational leadership lens. Results from this study indicated that dual-role administrators had time constraints in completing their job responsibilities, valued relationships with students, staff, and school board members; and utilized a team approach to manage school districts. Results also indicated supportive leadership behaviors aligned with principal responsibilities, while directive leadership behaviors aligned with superintendent responsibilities. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]